N-(2-Ethoxyphenyl)formamide

The title compound, C9H11NO2, was obtained as an unexpected product in an attempt to synthesize a triazene ligand. The title molecule is almost planar, with the formamide and ethoxy groups oriented at 2.7 (3) and 12.9 (2)°, respectively, with respect to the mean plane of the benzene ring. In the crystal, molecules are linked by intermolecular N—H⋯O hydrogen bonds, forming a chain along the a axis. Weak C—H⋯π interactions with an H⋯π distance of 2.78 Å reinforce the crystal packing, resulting in a three-dimensional network.

The title compound, C 9 H 11 NO 2 , was obtained as an unexpected product in an attempt to synthesize a triazene ligand. The title molecule is almost planar, with the formamide and ethoxy groups oriented at 2.7 (3) and 12.9 (2) , respectively, with respect to the mean plane of the benzene ring. In the crystal, molecules are linked by intermolecular N-HÁ Á ÁO hydrogen bonds, forming a chain along the a axis. Weak C-HÁ Á Á interactions with an HÁ Á Á distance of 2.78 Å reinforce the crystal packing, resulting in a three-dimensional network.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2505).
However, the title compound was formed as an unexpected product in an attempt for the synthesis of a triazene ligand, 1-(2methylphenyl)-3(2-ethoxyphenyl)triazene). In this article, we report the synthesis and crystal structure of the title compound.
The title molecule ( Fig. 1) is almost planar with formamide and ethoxy groups oriented at 2.7 (3) and 12.9 (2)°, respectively, with respect to the mean-plane of the benzene ring. The bond lengths and angles in the title molecule are in accord with the corresponding bond lengths and angles reported in a few similar structures (Landman et al., 2011;Chitanda et al., 2008;Hu et al., 2010).
In the crystal structure molecules are linked by intermolecular N-H···O hydrogen bonds (Table 1) to form a chain along the a-axis. Weak edge-to-face C-H···Cg1 stacking interaction between an ethoxy hydrogen and a benzene ring with H···π distance of 2.78 Å, (Cg1 is the center of benzene ring atoms C3/C4/C6-C9) reinforce the crystal packing resulting in a three-dimensional network (Fig. 2).

Experimental
The title compound was obtained as an unexpected product in an attempt for the synthesis of a triazene ligand, 1-(2-methylphenyl)-3(2-ethoxyphenyl)triazene). A 100 ml flask was charged with 10 g of ice and 15 ml of water and then cooled to 273 K in an ice-bath. To this were added 2-methylaniline (0.215 g, 2 mmol), hydrochloric acid (36.5%, 2 mmol) and 2 ml water. To this solution was then added a solution containing NaNO 2 (0.16 g, 2 mmol) in 2 ml water during a 15 min period.
After mixing for 15 min, the obtained solution was added to a solution of o-phenetidin (0.261 ml, 2 mmol), 2 ml methanol and 2 ml water. After that a solution containing sodium acetate (2.95 g, 36 mmol) in 10 ml water was added. After mixing for 24 h the colorless material was filtered off and dissolved in DMSO. By recrystallization from DMSO, the crystals of the title compound were obtained instead of the expected triazene.

Refinement
The H atoms were placed in calculated positions and refined as riding, with N-H = 0.86 Å and C-H = 0.93, 0.96 and 0.97 Å for aryl, methy and methylene type H-atoms, respectively, with U iso (H) = 1.2-1.5 U eq (C/N).
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.